(+/-)-trans-11-methyl-2,3-dihydroxy-6a,7,8,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline hydrobromide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (+/-)-trans-11-methyl-2,3-dihydroxy-6a,7,8,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline hydrobromide
• 英文别名: 11-methyl-2,3-dihydroxy-6a,7,8,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline hydrobromide；(6aS,12bR)-11-methyl-6a,7,8,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline-2,3-diol;hydrobromide
• 化学式: BrH*C₁₇H₁₇NO₃
• 分子量: 364.239
• InChiKey: AGDCTLQHMOQXJF-UFIUYGHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-苯并二氧戊环-5-基乙酸酯 在 盐酸 、 苯酐 、 正丁基锂 、 硼烷四氢呋喃络合物 、 水 、 三溴化硼 、 四氯化锡 、 二正丁胺 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 211.67h， 生成 (+/-)-trans-11-methyl-2,3-dihydroxy-6a,7,8,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline hydrobromide
  参考文献：
  名称：

  Analogues of doxanthrine reveal differences between the dopamine D1 receptor binding properties of chromanoisoquinolines and hexahydrobenzo[a]phenanthridines

  摘要：

  Efforts to develop selective agonists for dopamine D-1-like receptors led to the discovery of dihydrexidine and doxanthrine, two bioisosteric [beta-phenyldopamine-type full agonist ligands that display selectivity and potency at D-1-like receptors. We report herein an improved methodology for the synthesis of substituted chromanoisoquinolines (doxanthrine derivatives) and the evaluation of several new compounds for their ability to bind to D-1- and D-2-like receptors. Identical pendant phenyl ring substitutions on the dihydrexidine and doxanthrine templates surprisingly led to different effects on D-1-like receptor binding, suggesting important differences between the interactions of these ligands with the D-1 receptor. We propose, based on the biological results and molecular modeling studies, that slight conformational differences between the tetralin and chroman-based compounds lead to a shift in the location of the pendant ring substituents within the receptor. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.11.039

文献信息

• TRANS-FUSED CHROMENOISOQUINOLINES SYNTHESIS AND METHODS FOR USE
  申请人：Nichols David

  公开号：US20090030025A1

  公开（公告）日：2009-01-29

  Optionally substituted chromenoisoquinolines and analogs and derivatives thereof are described herein. In addition, syntheses of these compounds are described herein. In addition, uses of these compounds as dopamine receptor binding compounds are described herein.

  本文描述了可选地替代的咔唑啉和类似物及其衍生物。此外，本文还描述了这些化合物的合成方法。此外，本文还描述了这些化合物作为多巴胺受体结合化合物的用途。
• Analogues of doxanthrine reveal differences between the dopamine D1 receptor binding properties of chromanoisoquinolines and hexahydrobenzo[a]phenanthridines
  作者：Juan Pablo Cueva、Benjamin R. Chemel、Jose I. Juncosa、Markus A. Lill、Val J. Watts、David E. Nichols

  DOI：10.1016/j.ejmech.2011.11.039

  日期：2012.2

  Efforts to develop selective agonists for dopamine D-1-like receptors led to the discovery of dihydrexidine and doxanthrine, two bioisosteric [beta-phenyldopamine-type full agonist ligands that display selectivity and potency at D-1-like receptors. We report herein an improved methodology for the synthesis of substituted chromanoisoquinolines (doxanthrine derivatives) and the evaluation of several new compounds for their ability to bind to D-1- and D-2-like receptors. Identical pendant phenyl ring substitutions on the dihydrexidine and doxanthrine templates surprisingly led to different effects on D-1-like receptor binding, suggesting important differences between the interactions of these ligands with the D-1 receptor. We propose, based on the biological results and molecular modeling studies, that slight conformational differences between the tetralin and chroman-based compounds lead to a shift in the location of the pendant ring substituents within the receptor. (C) 2011 Elsevier Masson SAS. All rights reserved.